Gregory is in his first season with the Lincoln Saltdogs after spending parts of 2018 and 2019 with the Fargo-Moorhead RedHawks. A St. Cloud, Minn. native, Gregory also attended St. Cloud State University over four seasons before making his professional debut with the River City Rascals of the Frontier League in 2016. Gregory also pitched for the Rascals in 2017 before the RedHawks signed him ahead of the 2018 season. With the RedHawks in ’18, Gregory went 3-5 with a 4.34 ERA over 24 appearances and five starts, used primarily in long relief (74.2 innings in total).